7-(s-triazinylamino)-3-aryl-coumarin brightening agents



United States Patent 1 3,244,711 7 -(s-TRIAZINYLAMINO)-3-ARYL-COUMARIN BRIGHTENING AGENTS Otto Bercndes and Heinrich Gold, Cologne-stammheim, and Carl-Wolfgang Schellhammer, Opl'aden, Germany, assignors to Farbenfabriken Bayer Aktiengesellschaft, Leverkusen, Germany, a corporation of Germany No Drawing. Filed May 12, 1965, Ser. No. 455,290 Claims priority, applictigg (git-many, May 23, 1964,

in which R denotes hydrogen, a lower alkyl radical, such as methyl or ethyl, a lower alkoxy group, such as methoxy or ethoxy, or halogen, especially chlonne, and R means an alkyl, alkenyl, cycloal-kyl, aralkyl or aryl rad-1- cal, while X stands for chlorine or for the group 0R where R denotes an alkyl, alkenyl, cycloalkyl, aral'kyl or aryl radical.

The coumarin compounds of the above formula are suitable for brightening a great variety of materials, for example, for brightening textile materials of cellulose ester fibres and also polyamide, polyurethane, polyacrylonitrile and polyester fibres, furthermore for brightemng leather and soaps; they are especially well suited for brightening synthetic resins, e.g. of polyvinyl chloride, and for brightening lacquers of cellulose esters or nitrocellulose.

The brightening agents of the present invention can be applied in the usual manner, either in the form of solutions in organic solvents or in the form of solutions or dispersions in water. The brightening agents can also be incorporated with casting or spinning masses which serve for the production of synthetic articles, such as toils, fibres, filaments, and the like. The amounts required for brightening can vary within wide limits and can easily be determined by preliminary experiments and lie, in general, far below 1%, referred to the weight of the material to be brightened.

Some of the coumar-in compounds of the above general formula, which are to be used as brightening agents, are listed in the following table by way of example:

TABLE --N N NH 0 Melting R1 0R1 X point inC.

(a)- H OC2H5 C1 230 (b) H ooHwHm o1 215 (c)--- H OCH2CH2OCH3 01 165 (d) H OCHZ-CH=OH2 o1- 218 (e) H OCHZCGHS c1--. 19s (1 H OCH2C1I2OCH3 OCH2CHZOCHQ 154-157 (g)..- H OCH(CH3)2 oomonm 209-212 (h)- 1-1 OCHZOH2OCH3- OOHzCH2CH2CHa; 143-145 (1)... H OCHzCH=CHz OCH2CH=CHz 190 (k).-- 0113* OCH -CH=CH.-- o1 230-231 1 01* ooH2-cH=oH, o1 273 *In 4-p0sition.

The 7-(s-triazinylamino)-'3-aryl-couma1in compounds are obtainable, for example, by condensing 1 mol cyanuric chloride with 1 mol 7-amino-3-aryl-cournarin and 1 or 2 mol of an alcohol, alkenol, cycloalkanol, aral-kanol or phenol, in any sequence and in known manner, in the presence of an acid-binding agent.

In comparison with the already known brightening agents, the 7-(s-triazi-nylamino)-3-aryl-coumarin compounds of the general formula in which R and X have the meaning given above, while R and R stand for hydrogen or hydrocarbon radicals, the brightening agents of the present invention are superior in that they lead to brightening effects which are faster to light and less greenish.

The following examples serve to illustrate the invention Without, however, limiting its scope.

Example 1 1 gram of one of the coumarin compounds listed in the table under (e), f) and (-g) is incorporated on a roller with 1000 g. of opaque soft polyvinyl chloride. The material is then excellently brightened and exhibits a neutral White shade.

Example 2 1 gram of one of the cou-marin compounds listed in the table under (c) and (d) is dissolved in 1000 g. of a colourless lacquer of cellulose acetate or nitrocellulose. T-he lacquer is then thinly spread on a colourless primary coat. After drying, the lacquer film is excellently brightened.

Example 3 A fabric of polyamide fibres is introduced in a liquorto-goods ratio of 40:1 into an aqueous bath which contains, per litre, 1 g. oleyl sulphonate, 0.75 g. formic acid and 0.1 g. of the conmarin compound listed in the table under d). The bath is then heated to -95 C. and kept at this temperature for 30-60 minutes, while the fabric is moderately moved about in the bath. The fabric is subsequently rinsed and dried. The textile material thus treated exhibits a very good neutral brightening effect.

Example 4 A fabric of cellulose acetate fibres is treated at 60 C. in the manner described in Example 3, but with the difference that the bath contains one of the cou-marin compound-s listed in the table under (0) and (f), instead of the coumarin compound listed under (d). The textile material thus treated exhibits a very good brightening effect.

We claim:

1. A compound of the formula in which R is a member selected from the group consisting of hydrogen, lower alkyl, and chloro; R is a member selected from the group consisting of lower alkyl, beta lower alkoxy lower alkyl, lower alkenyl, and phenylsubstituted lower alkyl; and X is a member selected from 3 i 4 the group consisting of chloro and -OR wherein R 7 is a member selected from the group consisting of lower GH O 011201120 alkyl, lower alkenyl, and beta lower aikoxy alkyl. N V

2. A compound of the formula N r Y 5 CH OCH CH O CHaOCHzCHz 3 2 N 5. A compound of the formula N/ (onmcno 01 I I N NH O/-O 3. A compound of the formula N (C a)2CHO C5H5CH2O Q 15 References Cited by the Examiner I UNITED STATES PATENTS V of 2,945,033 7/1960 Hauserman-n 260-2475 WALTER A. MO*DANCE, Primary Examiner. 4. A compound of -the formula I. M. FORD; Assistant Examiner. 

1. A COMPOUND OF THE FORMULA 